


fifth date’s a charm

by theyellowumbrella



Category: Happy Endings (TV)
Genre: Backstory, F/M, Gen, Pre-Series, college for the most part
Language: English
Status: Completed
Published: 2014-05-10
Updated: 2014-05-10
Packaged: 2018-01-24 06:59:42
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,337
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1595813
Author URL: https://archiveofourown.org/users/theyellowumbrella/pseuds/theyellowumbrella
Summary: <blockquote class="userstuff">
              <p>The history of Max and Penny. (More like how Penny fell in love with a gay guy and never really fell out of it).</p>
            </blockquote>





	fifth date’s a charm

**Author's Note:**

> I’ve just started watching _Happy Endings_ and I hate that it was cancelled, but at least I can write the kind of unknown history of Max/Penny. (If anything about them was revealed past the episode _The Shrink, The Dare, Her Date and Her Brother_ , I’m sorry but that’s the point I’m at right now). I never really thought she got 100% over him, so here you go. I hope the remaining _Happy Endings_ fans enjoy this.

“So, have you heard who your new roommate’s gonna be?” Penny asks Dave as she paints her toenails, not looking up from the blur of magenta that she’s applying to her toes.

 

“Uh, yeah, his name’s Max,” he answers vaguely as he flips through his textbook, making notes here and there.

“Ooh, is he cute?” she asks, expecting her straight friend to know if his new roommate that he’s never met is cute. You know, rational best friend stuff.

 

He looks up and sends Penny an exasperated look before saying, “I don’t know!”

 

“Well, you could easily just—”

 

They’re interrupted by the door opening, revealing a tall guy around their age holding two suitcases and a box. He’s wearing a plaid shirt and a white t-shirt with a pair of uneven-at-the-edges jeans that would normally make any other guy look scruffy and would be a total turn-off, but damn, is he fine.

 

There’s some stubble on his chin and some that could make up to a moustache, but you can only notice it if you look properly at him, which she currently is. “Hey, I’m Max,” he says, reaching out to shake Dave’s hand.

 

“Dave,” he says in return, then goes back to reading.

 

“And you are?” he asks Penny, who’s dropped the small glass bottle of magenta nail polish onto the bed and is staring at him with her mouth agape.

 

“I’m Penny,” she finally manages to get out, before coughing on her own words, if that’s possible.

 

“Oh... um, your nail polish is spilling,” Max says, pointing to the dripping pool of pink nail polish.

 

She smiles widely, trying desperately to hide her embarrassment. “Oh. Well... this is Dave’s bed, anyway.” She turns to her friend and says, “Oh, by the way, Dave, Alex stopped by. She said that she’d love to go on another date and that you should either call her or ask Jane to set it up because she’ll probably end up forgetting anyway.”

 

“Who’s Alex?” Max asks as he unzips his suitcases and throws them anywhere he can see.

 

“She’s my friend’s girlfriend’s sister,” Dave says with a hint of a smile. “We’ve been on a couple of dates.”

 

“Oh, cool,” he says, dumping a pile of books onto an empty piece of floor.

 

“You know, you have cupboards for that,” Penny points out.

 

“Yeah,” he says, shrugging.

 

-

 

On their first date, Max takes her out for pizza and drinks at this new restaurant that just opened. When she leans in to kiss him goodnight, he hugs her real tight instead.

 

-

 

Their second date is a triple date with Brad and Jane and Alex and Dave which inevitably goes horribly, as expected by them all. It’s the first time that Max gets to meet them all at once, which probably wasn’t a great idea in retrospect. Jane gets all weird about a spelling error on the menus, and then when Alex says ‘bajillion’ about a dozen times, she snaps and shouts, “It’s not a real word!” Then, Dave bursts into song, Jane has an allergic reaction to seafood, Brad somehow convinces Max that he’s super gay and Jane’s his beard and Penny sings the whole score of Peter Pan in falsetto. Needless to say, there’s no goodnight kiss again.

 

-

 

They actually have a third date, which is a big surprise to Penny. He asks her out when they‘re all hanging out—and by all, I mean all six of them. Everyone aws when he comes right out and asks, “Hey, Pen, you wanna go out on Saturday?”

 

In Penny’s experience, this is usually the night that they have sex for the first time, but instead, all that she gets is a kiss on the cheek. Baby steps, she tells herself.

 

-

 

Their fourth date is to a party that Alex and Dave are co-throwing, and this time, he kisses her. On the lips. He’s drunk and it’s only for about half-a-second, but his lips brush against hers and there are about four hundred other students there to witness it.

 

-

 

On their fifth date, he takes her to the Sears Tower and when she gets cold, he’s a real gentleman and gives her his coat despite the fact that his teeth are chattering.

 

“Why haven’t we kissed yet?” she finally manages to ask when they’re on the seventy-third story.

 

“We kissed at the party,” he says, avoiding the question.

 

“Besides that.”

 

“I don’t know.” He can’t think of a good enough excuse, so he just tells her half of the truth. Not the whole ‘I think I’m gay’ thing, but the less crushing version. “I didn’t think it was the right time. Our first date was fun, but it didn’t feel right, and our second date... well, that’s pretty self-explanatory, our third date was me having a phone conversation with your mother because you forgot about your scheduled phone call, our fourth date, we did technically kiss.”

 

“And that brings us to tonight.”

 

“Yeah, it does,” he says. And then he does the most amazing thing in Penny’s eyes: he leans in, closes his eyes and kisses her.

 

-

 

After that, they decide to be boyfriend and girlfriend, which means he kisses her a lot now, and Penny seems to think that they’re super in love while Max is sort of... coming to terms with something in his life. But dating Penny has a lot of perks, actually. She’s more his best friend than his girlfriend, and she introduced him to Alex and Jane and Brad and Dave, no matter how crazy and fucked up they are, because he’s equally fucked up and crazy.

 

-

 

They lose their virginities to each other, and the whole time, Max is staring at a poster of Johnny Depp.

 

-

 

She first says “I love you” the September after they start dating. He first says it the August after they break up.

 

-

 

When they’re twenty-two and fresh out of college, Brad proposes to Jane. When they’re twenty-six and Brad and Jane have been married for three years, Dave proposes to Alex (“A three year engagement has trouble written all over it,” Max tells him a few days after Alex runs out on the wedding). They all look pitifully at Penny when Max turns up with a date to both of the events and she comes alone.

 

-

 

“Max!” Penny says, pulling her best friend into a hug. “I haven’t seen you in, like, forever!”

 

Max pulls away and goes back to playing his video game. “Pen, I saw you this morning.”

 

“So?” she asks, collapsing onto the remaining spot on the sofa. “Anyway, I was looking through a bunch of boxes that are in Alex and I’s shared garage-—” 

 

“Why do you have that?” he cuts in.

 

“Not important. Like I was saying, I was looking through the garage and I found this.” She produces a picture from her purse and hands it to Max, who’s pausing his game.

 

He smiles at the picture of twenty-year-old Max, Penny, Brad, Jane, Dave and seventeen-year-old Alex all sitting in Dave and Max’s dorm. “Hey, this was our six-month-aversary!”

 

“Yeah, back then we all thought it was so weird that Dave was dating a sixteen-year-old. Especially Jane.”

 

“No, I think Jane’s primary problem wasn’t the age, it was the sister of it all.”

 

“Po-tay-to, po-tah-to.”

 

-

 

“Are you in love with Max?” Alex blurts out one day when they’re hanging out together.

 

“What? No.”

 

“It’s okay if you are, y’know?”

 

“I know. But I’m not.”

 

Alex doesn’t really believe her, but she leaves it alone after that because Penny’s allowed to be in love with Max, even if he isn’t in love with her. And after that, everyone just leaves the topic alone because Penny really is over Max, even if it isn’t a hundred percent. They also don’t talk about how she hasn’t been in a serious relationship since Max broke it off with her, because it seems irrelevant now, and because she’s always so happy in his company that it doesn’t matter anymore.

**Author's Note:**

> I hope they weren’t too OOC, but I don’t have that great of a grasp on their characters yet (I’ve only been watching for like, a day).


End file.
